What Are You Waiting For?
by Drowningouttheglow
Summary: He finally realized what he should have known years ago in that one simple moment that changed everything. There was never going to be a right time and right place. What was he waiting for? Dean/Jo Oneshot.


**_What Are You Waiting For?_**

Disclaimer: I don't own Supernatural nor do I own these lyrics. Credit at the bottom.

* * *

_You'll sit alone forever_

_If you wait for the right time_

_What are you hoping for?_

* * *

Dean Winchester woke up at exactly 8:00 am at the motel that him and his brother Sam were staying at. They were in a new town each night and it almost got to the point where he would wake up not remembering where they were.

The sun was bright outside and there wasn't a cloud in the sky. Dean rubbed at his eyes and looked across the room to find Sam already awake happily pounding at his computer probably doing research on the Colt or God knows what.

"Hey," Sam said quickly, eyes still glued to the screen, "I woke up at around 5 and couldn't go back to sleep, so I decided to make good use of the time."

Dean rolled his eyes at his dorky little brother who openly enjoyed research. "Well that's just fantastic!" Dean replied sarcastically. "Why can't you just be looking at porn... Like the rest of us." He complained while swinging his legs over to the floor.

"And by 'the rest of us' you mean you?" Sam asked taunting his brother.

"Well if you put it that way, sure." Dean smirked as he headed towards the bathroom.

Dean and Sam kept up there usual ways of jokes and banter even though the Apocalypse was upon them and Lucifer was getting closer to ending the world. They were both extremely stressed out and tired, but neither talked about it. It was better that way, avoiding emotions in case anything were to happen.

When Dean got out of the shower and dressed, he joined Sam at the small table in the dilapidated room.

"Bobby called. He said that we should go to his place tonight now that we have the Colt. Ellen and Jo will be there," Sam said, "Oh, and Cas too, but he'll probably just appear out of thin air like he usually does."

Jo, Sam, and Dean had gotten their hands on the Colt, the night before from the demon, Crowley. Everything was set into place. Their team had the weapon to kill the devil and they knew his exact location. Their plan would be put into place tomorrow. This was their last day to finalize all the plans and they would be set.

With some luck on their side, the plan would go off without a hitch, but they knew it wouldn't be that easy. There was a huge possibility that tonight might be their last night on earth and it was good that they would be all spending it together.

The two cleaned out their room and prepared to leave. They grabbed their bags and headed to the door.

* * *

It was the stupidest idea that anyone had thought of that night. It beat getting Cas drunk and it even beat the idea of the two brothers facing Lucifer together. He saw her in the kitchen and maybe since the first time they met he saw her as more than just a little girl that needed protection. No, he saw her as the girl that he wanted to hit on "so hard it would make her head spin" that first night at the Roadhouse. She knew right away that is was just "the wrong place, wrong time" and that every single moment following that they shared together would always be caught at the wrong place and the wrong time.

Dean got up from the table that he was sitting at with Sam, and began to walk to the kitchen where Jo was getting another beer. Her hair was arranged in her usual soft, natural waves, which brought out the golden hues. She was wearing a pair of dark wash denim jeans that hugged her in all the right places and a simple black t shirt.

"So. Dangerous mission tomorrow. Guess it's time to eat, drink, and, you know, make merry." Dean said as he reached his destination leaning against the kitchen counter.

Jo could see the look in his eyes. It was the look of pure lust. It was different from any way that he had looked at her before. She decided to play it as cooly as possible. " Are you giving me the last night on Earth speech?"

"What?"

"What?"

This probably was the only time that Jo and Dean had ever been at a loss for words. Usually they would have both been at each other bickering like an old married couple or constantly bouncing off each other with something witty or flirty to say. This was different.

Dean decided to lay it all out on the table. "No...," he paused. "If I was, would that work?" he finished sounding a little more desperate than he wanted to let on.

That charm, the light freckles that sat on the bridge of his nose and cheeks, that damn smirk that made her want him so badly in the first place 3 years ago, it was all too much. Jo leaned in closer. Her hand drifted by his ear and to his neck. It was almost as if their lips brushed for just a moment, but she pulled away. The same old Jo came right back. She was the girl with the unbelievable attitude and strong will and most of all feisty remarks. "No," she replied with heavy breath. "Sweetheart, if this is our last night on Earth, then I'm going to spend it with a little thing I call self-respect."

She smiled, shaking her head slightly in disapproval, and walked away, back to Cas and her mother.

The way she walked away from Dean reminded him of the time that he and Sam had run into the Harvelle girl in Indiana planning on working the same job, getting rid of an angry spirit who had taken residence in the home of a couple with a baby on the way. They decided that they could finish the job faster if they worked together. Dean has spent most of the time watching Jo and protecting her at all costs, like her own little personal bodyguard. Dean and Jo were headed to the Impala where Sam was waiting to go local cemetery and burn the bones.

"Watch your step," Dean has insisted when they reached a break in the ground.

It was the point Jo had enough. "Really? What you think I'm going to fall and break myself?". She was pissed off and Dean knew it. "I'm not some fucking porcelain doll! You listen up Dean Winchester. I may be a girl, but I am not afraid to get my hands dirty and I'm certainly not in any need of protection. Out of all people I thought you would realize that. So you can take your concern and annoying comments and shove them straight up your ass."

"Jo... I just don't want you getting hurt," Dean told her. "Besides your mother would kill me if anything ever happened to you. "

She huffed. "Well don't you worry your pretty little face... I can handle myself." She lifted the right corner of her mouth into a slight smile forgiving him and turned her heel and walked towards the car. She began arguing with Sam about how she apparently had called shotgun earlier that day.

Dean didn't really remember much from that hunt. It was some subpar spirit poorly scaring some pregnant woman and her husband, nothing more. He did remember the way she told him off. People didn't speak to him like that unless it were Sam or Bobby. Mostly it was because they were intimidated, but Jo was fearless.

Some say there are defining moments in everything. The one precious point in time where everything changes. They remember the smell in the air, the taste in their mouths, the song on the radio, the weather, everything. That was Dean's. In that very moment that she turned him down and walked away with a kick to her step and all the confidence in the world just like she had on that hunt, he realized that Jo would never be just another girl. She couldn't just be another girl he picked up in some random town and slept with only to never see again. She had to be more.

Dean didn't sleep much that night with constant thoughts running through his head.

_What if I can't do this after all? T_houghts of doubt circled his mind. _What if I let everyone down and people die because of it? Sam. Bobby. Ellen. Jo_. His mind stopped.

Thinking about losing any of the people close to Dean was hard enough, but for some reason thinking about losing Jo was too hard to bare. He only saw her occasionally and it was mostly concerning business, but the thought of losing her and being left with the 'what ifs' and the 'what could have beens' was too difficult The loss and feeling of regret would make him shut down. And the last thing he ever wanted was regrets.

It was right then and there that he decided that after all this was over, he was going to make sure that no regrets were made. He would tell the girl with the golden hair how he felt and that he wanted to be with her. Be with her in every sense of the word- physically, emotionally. She could never be one of his usual one night stands. Dean was feeling things for Jo that he had never felt for anyone in his entire life and he had no idea why this was all buried for three long years.

* * *

When morning came, the house was silent. Much different from the party that had occurred the night before. They were all nervous and scared and anxious, but nobody said anything. Words weren't necessary when the thoughts were clearing visible on everyone's faces.

They loaded up the cars. Dean and Sam in the Impala and Ellen, Jo and Cas in Ellen's station wagon.

When they reached the town they all knew something was wrong. Something was definitely wrong. There were no people, no demons, nothing. Just a town that was beginning to look like a ghost town from an old Western movie. Cas decided to go and try to see what had happened or what was happening. After a moment past, they all saw a figure in the distant. It was Meg, the demon who had tried to kill the brothers several times before. This made them all nervous for the simple fact that she always had a trick up her sleeve and she always had a back up plan.

Everything after that seemed to pass Dean by in a flash forward sense. Everything moved so fast around him. Mostly it was a way to cope, not being able to believe what was happening.

This time was no exception to Meg's crafty ways. She had brought her 'pets' from the pit- the hellhounds. After she released the dogs on the four of them, Dean got dragged down. Jo being Jo ran back to help him because that was just the kind of person she was.

The brave girl fought several of them off, but her efforts weren't enough. From no where one of the beasts jumped on Jo and knocked her to the concrete road.

Dean saw everything. He saw that monster tear into Jo's perfect porcelain skin and he saw the look in her eyes as she screamed out in pain. He got to his feet, ran to her and picked her up. He carried her to a convenience store that was the nearest form of shelter and safe haven from the bloodthirsty dogs that were after them. Ellen and Sam followed right behind them.

Blood. There was blood everywhere pouring from her side. They did the best they could, covering it with an Ace bandage to keep her from losing anymore. Sam knew that Jo was dying and Dean knew too, he just didn't want to admit it. His worst nightmare was coming true and the worst part was that there was nothing he could've done to stop it.

"We gotta get her out of here," Dean said to Sam hoping Jo was out of earshot. "We need a stretcher or something."

"Stop. Guys, stop," Jo interrupted. "Can we be realistic about this please. I can't move my legs. I can't be moved. My guts are being held in by an Ace bandage." She held her breath for a moment, "We gotta get our priorities straight here. Number one I'm not going anywhere."

"Joanna Beth, you stop talking like that," Ellen scolded mad at the fact that her daughter was becoming okay with the fact that death was near for her.

"Mom. I can't fight. I can't walk. But I can do something." Jo looked down, "We got propane, wiring, rock salt, iron nails, everything we need."

Sam not quite sure what she meant responded, "Everything we need?"

"To build a bomb Sam," Jo retorted strongly.

Dean's heart sank. "No, Jo, no," he managed to say. It was surprising he managed to say anything at all.

"You got another plan? You got any other plan?" she asked knowing that he didn't. "Those are hellhounds out there, Dean. They got all of our scents. Those bitches will never stop coming after you. We let the dogs in, you guys hit the roof, make a break for the building next door I can wait here with my finger on the button." She was speaking with no depth in her voice, no emotion. If she cried right then and there it would have only made things worse, harder. "Rip those mutts a new one," she joked. "or at least get you a few minutes head start anyway. If I can get us a shot on the devil." Dean shook his head. "Dean, we have to take it."

"No!" Ellen cut in.

Jo looked at her mother. The woman who only wanted to protect her daughter, never wanting her to get hurt. "Mom, this might literally be your last chance to treat me as an adult. You might wanna take it.

Ellen sat in silence for a moment. She swallowed hard and looked to the boys, "Well you heard her. Get to work."

Sam and Dean immediately got to work collecting the materials they needed. They set the bomb up around Jo who was sitting, leaning up against the wall. In about five minutes all the wires were connected to a small button that would set off the bomb and destroy the small store killing everyone and everything inside.

Sam said his goodbye first. He squeezed Jo's hand and smiled at her. He got up and went to go talk to Ellen.

Dean approached the girl on the ground and knelt down next to her. He spoke softly, "Okay this is it." Dean took Jo's bloodstained hand and gently placed the button in it. "I'll see you on the other side. Probably sooner than later."

Jo forced a smile as best she could, "Make it later?"

He held his hand there just holding her's, lightly squeezing it, not wanting to let it go.

He looked up from their hands and into her eyes. She had been crying and her cheeks were gently stained. She was dying and she was still perfectly beautiful as she always was. Tears began to form in his own eyes giving them a glassy appearance and her's did the same.

Dean grabbed Jo's head, smoothed her light hair out of her face, and pulled her towards him kissing her forehead. She tried not to cry, she really did, but tears came streaming down her face.

He pulled away and once again looked into her big brown eyes. He couldn't help himself. Before either of them even knew what was happening, his lips were on hers. He was kissing her because he needed her, because he couldn't let her go, because he loved her.

They pressed their foreheads together and just held themselves in that moment. Dean wished it could have lasted forever. "Okay," he sighed as he distanced himself from her. He pulled himself away because if he had anymore contact with her, he would lose it and a crying and emotional Dean was the last thing anyone needed right now.

It was then Ellen decided she couldn't leave her daughter, her Joanna Beth. She looked at Jo and she knew exactly what her mom was thinking. "Somebody's gotta let them in and like you said you're not going anywhere." She would let the hounds in and hold her daughter when the bomb went off. There was no talking her out of it. She was a Harvelle woman- strong-willed. If Jo would be going down, they would be going down together.

"Get going, boys," Ellen said to the brothers, eyes still on her daughter.

"Ellen..." Dean responded.

"I said go." They both knew there was no changing her mind so they did what exactly what she told them to do.

Ellen stopped, and said one last thing, "And Dean, kick it in the ass... Don't miss.". Dean nodded knowing that this was what he has to do. He swallowed hard and turned to leave.

And with that the two left using the fire exit. Sam went first, Dean following shortly behind. They climbed down the metal stairs as fast as they possibly could. Once they reached the bottom Dean stopped for a moment, having second thoughts about leaving Jo and Ellen behind.

"Dean we gotta go! Ellen can only wait so long to set it off," Sam yelled. He was about five yards ahead of his older brother. Dean stood there until he finally put the bigger picture on his mind and ran to catch up to Sam.

He waited too long, standing there, thinking of possibly the greatest regret of his life. Before Dean knew there was a flash of light.

_Boom._

* * *

Dean woke up at exactly 8:00 am. He shot out of bed and gasped for air, expecting to still be in the abandoned town with Sam next to him, Cas missing, and Ellen and Jo dead, but that wasn't the case.

Sweating, he looked and saw the same Sam as the day before on his computer.

"What the hell is going on!?" Dean yelled confused and in horror.

Sam jumped, "Geez, man sorry if I woke you. I've been up sin-"

Dean quickly cut his brother off, "Lemme guess you've been up since 5 and you couldn't go back to sleep, so you decided to make good use of the time?"

"...Actually yeah, that's exactly what I was going to say," Sam replied trying to make sense of the current situation. "Wait, how the hell did you know that?"

"I have no idea, all I know is that I think this day has happened before."

"We'll figure this out, but Bobby called and we're all meeting at his house tonight: you, me, Cas, Ellen, and Jo."

_Jo._

Dean stopped breathing for a second. Hearing Jo's name. "Is she o- okay?"

"What?" Sam said absentmindedly.

He raised his voice, "Is Jo okay?! Is she alright?!"

It startled Sam taking him aback, "Yes, yes! She's fine. You'll see her tonight! Dammit Dean, calm down."

There was only one possible explanation for this madness. Castiel. He had sent Dean to the 70s before, of course he could send him back a day, reverse time before the hellhounds happened, before the explosion happened. Dean left the motel room and paced on the walkway. Before he even knew it, Cas appeared in front of him.

"I knew it!" Dean yelled as he threw his hands in the air. "What the hell was that? A dream? Reality? Some fucked up alternate universe?"

"Oh well hello to you too, Dean." Cas was beginning to catch on to how useful sarcasm was. "That was real. Everything that happened tomorrow was real. I simply reversed time. You're the only one who remembers anything."

"So the point of this all was so I could get a sneak peak on what not to do? So I can relive the torture all over again?" Tears began to well up in his eyes. "She died because of me, Cas! I let her die."

"And she still is going to die," The angel interrupted his friend. "Like I told you before Dean, destiny can't be changed, but you can change what happens before hand. You deserve to tell Joanna how you feel." Dean opened his mouth prepared to say something in his defense, but Cas stopped him. "Don't try to deny it. I'm an angel, not an idiot."

Dean conceded. "Thank you."

"Now you better not screw this up because I'm not giving you a third chance." And just like he came, Castiel left in a blink of an eye.

Dean knew he had a second chance. A second chance to make things right and tell Jo the things that he should of told her years ago. There was never was going to be a right time or a right place. What was he waiting for?

Dean pulled his phone from his pocket, hands shaking and found Jo in his contacts. He held the phone close to his ear as he heard it ring. "Pick up, please," he muttered under his breath.

"Hey this is Jo. Leave a message and maybe I'll get back to you!" her voice chimed in as the call went to voicemail.

_Beep_.

"Hey Jo, it's Dean... I just I need to see you... Um.. I want to tell you something, " he paused unsure of how to go on, "Scratch that, I _need_ to tell you something. I can't go into this thing tomorrow with any regrets. So call me back when you can or I guess I'll just see you tonight."

All the paths would lead to Jo's death, it was inevitable, but a different path could be chosen. All he could do was change the things he said to the girl he loved her last night on earth. He didn't want her to die. It would be one of the hardest things he had to face, but he would do it with no regrets. What was he waiting for?

**A/N: Wow, okay there was my first fic. I'm totally new to this so tell me what you think... If you actually read it. Seriously if you did bonus points to you. I reworked the ending like three times and I finally have it to how I like it and how it actually makes sense. The idea came to me after watching 5x10 being really pissed off about it and also the song 23 by Jimmy Eat World. The lyrics are up there. The ending with the voicemail idea completely goes to 'beyondwonder.' **


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